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Our top choices for Sheffield hotels

Wilder House Berkshires

Wilder House Berkshires
2.0 star property
Sheffield
9.8 out of 10, Exceptional, (43 reviews)
  • cleanliness
    Unwind in the Berkshires at this charming B&B with free weekend breakfast.
"Clean, cute, private, nice location. Breakfast was wonderful. Great value as well. Would definitely go back. "
United States
Kristinna
The price is Rp3.246.800
Rp3.626.676 total
includes taxes & fees
19 Feb - 20 Feb
Wilder House Berkshires

Holiday Inn Express Hotel & Suites Great Barrington by IHG

Holiday Inn Express Hotel & Suites Great Barrington by IHG
2.5 star property
Great Barrington
8.8 out of 10, Excellent, (731 reviews)
  • cleanliness
    Unwind in the Berkshires with indoor pool and free hot breakfast each morning.
"Great property, very accommodating. "
United States
Shanice
The price is Rp1.802.094
Rp2.012.939 total
includes taxes & fees
8 Mar - 9 Mar
Holiday Inn Express Hotel & Suites Great Barrington by IHG

Prospect Berkshires

Prospect Berkshires
3.0 star property
Egremont
9.6 out of 10, Exceptional, (19 reviews)
  • cleanliness
    Contemporary Berkshires retreat with mountain views and indulgent spa services.
"Excellent local stay - would recommend to all"
United States
Gentian
The price is Rp3.301.032
Rp4.251.594 total
includes taxes & fees
9 Mar - 10 Mar
Prospect Berkshires

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
2.5 star property
Great Barrington
9.4 out of 10, Exceptional, (766 reviews)
  • cleanliness
    Rest in a peaceful Berkshires retreat with a fitness centre and indoor pool.
"Very friendly staff. Clean rooms. Great breakfast variety. Would definitely stay again."
United States
Dinh
The price is Rp2.543.142
Rp2.840.689 total
includes taxes & fees
11 Feb - 12 Feb
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

Locust Tree Bed and Breakfast LLC

Locust Tree Bed and Breakfast LLC
3.0 star property
East Canaan
9.0 out of 10, Wonderful, (414 reviews)
  • cleanliness
    Experience the charming Locust Tree B&B in East Canaan with free breakfast.
"Great breakfast! Had a wonderful stay!"
United States
Michelle
The price is Rp1.768.410
Rp2.033.672 total
includes taxes & fees
8 Feb - 9 Feb
Locust Tree Bed and Breakfast LLC

Gedney Farm

Gedney Farm
3.5 star property
Great Barrington
9.2 out of 10, Wonderful, (135 reviews)
  • cleanliness
    Elegant Berkshires retreat with on-site dining and lush garden views awaits.
"We loved our stay at Gedney. Michael was a sweetheart, and the grounds are GORGEOUS. We loved our room with fireplace - the whole setting is just country and updated/old. For anyone who loves farms and barns and rustic, this is for you. Can't wait to return."
United States
Lynda
The price is Rp3.124.022
Rp3.427.052 total
includes taxes & fees
17 Feb - 18 Feb
Gedney Farm

The Old Inn On The Green

The Old Inn On The Green
4.0 star property
Great Barrington
9.2 out of 10, Wonderful, (90 reviews)
  • cleanliness
    Dine among candlelight at this charming Great Barrington inn with a seasonal pool.
"Beautiful Inn and outstanding chef"
United States
Catherine
The price is Rp5.136.810
Rp6.198.698 total
includes taxes & fees
17 Feb - 18 Feb
The Old Inn On The Green

Quality Inn Great Barrington

Quality Inn Great Barrington
2.5 star property
Great Barrington
8.4 out of 10, Very good, (1,001 reviews)
  • cleanliness
    Experience a peaceful stay near Mahaiwe Performing Arts Centre.
"This was a perfect place to stay. Reasonably priced, very clean, and the young lady who worked the front desk in the evening was super friendly. We will definitely book here again. "
United States
Jerome
The price is Rp1.274.097
Rp1.423.166 total
includes taxes & fees
8 Mar - 9 Mar
Quality Inn Great Barrington

Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (830 reviews)
  • cleanliness
    Experience the beauty of the Berkshires at a cosy lodge with golf access and pool.
"Very comfortable and very close to ski slope and restaurants"
United States
Frederick
The price is Rp1.662.052
Rp2.232.762 total
includes taxes & fees
11 Feb - 12 Feb
Berkshire Mountain Lodge

Monument Mountain Motel

Monument Mountain Motel
2.5 star property
Great Barrington
9.0 out of 10, Wonderful, (819 reviews)
"The room was clean, and the staff was friendly and helpful. "
United States
Damien
Monument Mountain Motel

Blackberry River Inn

Blackberry River Inn
3.0 star property
Norfolk
9.4 out of 10, Exceptional, (168 reviews)
  • cleanliness
    Serene New England escape offers tranquil country setting with seasonal pool.
"Courteous welcoming staff, amazing breakfast, and restful stay, highly recommend."
United States
Paulina
The price is Rp2.767.983
Rp3.183.181 total
includes taxes & fees
12 Feb - 13 Feb
Blackberry River Inn

Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
2.5 star property
Pittsfield
9.2 out of 10, Wonderful, (81 reviews)
  • cleanliness
    Relax in the heart of the Berkshires with an indoor pool and hot tub after a day out.
"it was a lovely hotel, hot tub was perfect after the day of skiing, everything very clean and new and lovely breakfast. All staff were very nice."
United States
Laura Pearson
The price is Rp2.223.986
Rp2.484.192 total
includes taxes & fees
10 Mar - 11 Mar
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

The Millerton Inn

The Millerton Inn
2.0 star property
Millerton
8.0 out of 10, Very good, (13 reviews)
  • cleanliness
    Escape to a Mediterranean culinary gem in historic Millerton with complimentary perks.
"Antonia was wonderful and made our stay special. She was kind and warm and when we were initially unhappy with our room immediately rectified the situation and in the end our stay was perfect! It’s a charming hotel, clean and centrally located, walking distance to all the local shops in town."
United States
Jamie
The price is Rp2.714.762
Rp3.071.074 total
includes taxes & fees
22 Feb - 23 Feb
The Millerton Inn

Hilton Garden Inn Lenox Pittsfield

Hilton Garden Inn Lenox Pittsfield
3.0 star property
Pittsfield
9.2 out of 10, Wonderful, (665 reviews)
  • cleanliness
    Perfect setting for a Berkshires visit with an indoor pool and Asian dining.
" Nice staff - beautiful hotel!"
United States
MARY
The price is Rp2.313.362
Rp2.584.025 total
includes taxes & fees
27 Feb - 28 Feb
Hilton Garden Inn Lenox Pittsfield

Shaker Mill Inn

Shaker Mill Inn
2.5 star property
West Stockbridge
9.6 out of 10, Exceptional, (445 reviews)
  • cleanliness
    Enjoy a relaxing Berkshires retreat with free breakfast and parking amenities.
"The large kitchen and sitting/living with gas fireplace, with adjacent separate bedroom was very clean and cozy. Thank you to Meg and Dan for providing a nice holiday stay!!!"
United States
Carin
The price is Rp1.873.236
Rp2.054.939 total
includes taxes & fees
8 Feb - 9 Feb
Shaker Mill Inn

Interlaken Inn & Resort

Interlaken Inn & Resort
3.5 star property
Lakeville
8.2 out of 10, Very good, (278 reviews)
  • cleanliness
    Lakeside resort with golf course access and seasonal outdoor pool offers a serene escape.
"Great"
United States
Jorge
The price is Rp3.016.402
Rp3.468.862 total
includes taxes & fees
18 Feb - 19 Feb
Interlaken Inn & Resort

Hampton Inn & Suites Berkshires-Lenox

Hampton Inn & Suites Berkshires-Lenox
2.5 star property
Lenox
9.2 out of 10, Wonderful, (1,000 reviews)
  • cleanliness
    Convenient Lenox hotel with indoor pool near Tanglewood Music Centre.
"The room and amenities were amazing. "
United States
Kathleen
The price is Rp2.011.619
Rp2.246.978 total
includes taxes & fees
1 Mar - 2 Mar
Hampton Inn & Suites Berkshires-Lenox

East Rock Inn

East Rock Inn
2.0 star property
Great Barrington
9.6 out of 10, Exceptional, (37 reviews)
  • cleanliness
    Experience scenic Berkshires at an inn with free parking and WiFi.
"The room was clean and comfortable wi will back next year:) "
United States
Nadya
The price is Rp2.198.673
Rp2.455.918 total
includes taxes & fees
22 Feb - 23 Feb
East Rock Inn

Berkshires Untold

Berkshires Untold
3.5 star property
Lenox
9.0 out of 10, Wonderful, (852 reviews)
  • cleanliness
    Experience Berkshires charm with on-site American dining and attentive service.
"So charming, clean, thoughtful touches and a really special place!"
United States
Juliana
The price is Rp1.489.982
Rp1.664.310 total
includes taxes & fees
8 Mar - 9 Mar
Berkshires Untold

Brook Farm Inn

Brook Farm Inn
3.5 star property
Lenox
9.4 out of 10, Exceptional, (164 reviews)
  • cleanliness
    Charming Berkshires B&B with outdoor pool near Tanglewood Music Centre.
"Everything was perfect - location and accommodation."
United States
Christopher
Brook Farm Inn
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Stay near popular Sheffield attractions

Learn more about Sheffield

Tucked in the Berkshires, this charming town offers scenic hikes at Bartholomew's Cobble and local art at the Sheffield Historical Society. Catch live performances at the Berkshire Theatre Festival in nearby Stockbridge or sample farm-fresh produce at the weekend farmers' market on the town green.

FTYTP1 The Upper Sheffield Covered Bridge, Sheffield, Massachusetts, USA

Top Sheffield Hotel Reviews

More cheap stays in Sheffield

Find out more about Sheffield

Top reasons to visit Sheffield

  • Outdoor Adventures: Sheffield is a haven for outdoor enthusiasts, offering skiing, hiking, and exploring picturesque lakes and nature reserves.
  • Family-Friendly Activities: Enjoy apple picking and exciting rides, making it ideal for memorable family outings.
  • Art and Culture: Discover a variety of art galleries that showcase local talent and creativity.
  • Charming Atmosphere: Experience the warmth of friendly locals and a welcoming community in the beautiful Berkshires.
  • Diverse Accommodation: From agritourism to cosy bed and breakfasts, Sheffield has unique stays catering to every traveller.

Find great hotels near Sheffield

Experience the charm of Sheffield, Massachusetts, with a variety of accommodation options that cater to every traveller's needs. From delightful agritourism properties to inviting bed and breakfasts, Sheffield offers pet-friendly and family-oriented stays perfect for your adventure. Explore nearby attractions while enjoying a comfortable retreat in this picturesque town, with additional options available in Great Barrington for an unforgettable holiday experience.

  • Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG: This charming 3.5-star resort offers a delightful blend of leisure and adventure, making it an ideal choice for families and business travellers alike. Nestled 19.3km from Sheffield, the resort features a variety of amenities, including an onsite mini-golf course, an arcade game room, and a playground to keep children entertained. The proximity to ski shuttles and lifts ensures that winter sports enthusiasts can easily access the slopes. With spacious accommodations and family-friendly services, this resort is perfect for a memorable vacation in the Berkshires.
  • Quality Inn: Located 9.7km from Sheffield, Quality Inn is the perfect base for adventure seekers and business travellers. Guests can enjoy a range of outdoor activities, from downhill skiing to hiking and biking, all available in the surrounding areas. The hotel’s focus on adventure sports makes it an exciting option for those looking to explore the natural beauty of the region. With comfortable lodging and easy access to recreational facilities, Quality Inn caters to those with an adventurous spirit while providing essential amenities for a productive stay.
  • Holiday Inn Express Hotel & Suites Great Barrington by IHG: Situated 11.3km from Sheffield, this hotel welcomes travellers with its inclusive atmosphere and modern comforts. Known for being LGBTQIA-friendly, it provides a warm environment for all guests. The property is well-equipped for business travel, featuring meeting spaces and complimentary Wi-Fi. Guests appreciate the contemporary design and convenient location, which offers easy access to local attractions. With attentive service and a focus on providing a comfortable experience, this hotel is an excellent choice for both leisure and business stays.

Where to stay near Sheffield

Sheffield, Massachusetts, offers an enchanting blend of adventure and history, perfect for an outdoor getaway. Nestled in the beautiful Berkshires, visitors can revel in stunning scenery, charming evenings, and a family-friendly atmosphere. Nearby attractions provide a romantic vibe, with friendly locals enhancing the experience. Whether you seek thrilling activities or a relaxing retreat, Sheffield and its surroundings promise a memorable stay, complemented by some of the best hotels in the region.

  • The Berkshires: Nestled 17.7km from Sheffield, The Berkshires is a stunning region renowned for its breathtaking outdoor experiences, making it a perfect destination for adventure seekers. With a blend of scenic mountains and serene lakes, this area is ideal for skiing in the winter and hiking in the summer. The Berkshires is not only about natural beauty—it's also home to various cultural events and venues, including conferences and festivals, which attract visitors year-round, particularly in the warmer months from June to August.
  • Great Barrington: Located 9.7km from Sheffield, Great Barrington is a vibrant city that draws visitors with its dynamic outdoor lifestyle and sporting opportunities. Known for its excellent skiing facilities, this area is a favourite among winter sports enthusiasts. During your visit, explore the local parks and lakes that offer tranquil spots for relaxation and picnicking. Great Barrington sees a peak in visitors from June to August, making it an exciting summer destination that balances adventure with community events.
  • South Egremont: Just 8.0km from Sheffield, South Egremont is a charming city that invites adventure lovers to experience its ski resorts and recreational activities. This area, like its neighbours, boasts stunning landscapes featuring mountains and lakes, perfect for both winter sports and summer excursions. South Egremont attracts a steady stream of visitors throughout the year, with a notable influx during the summer months. The nearby national state park offers additional opportunities for exploration and immersion in nature.

Things to do near Sheffield

Sheffield, Massachusetts, offers a delightful mix of outdoor adventures and family-friendly activities. Visitors can enjoy skiing at local resorts, partake in apple picking, and explore various art galleries. The area is perfect for day trips and exciting rides, making it an ideal destination for memorable family outings amidst the beautiful New England scenery.

Shopping

In Sheffield, you can enjoy shopping at local gems like Hoffman's Pottery for unique items. If you're up for a drive, Lee Premium Outlets, located 22.5km away, offers a variety of brand-name stores, while the Berkshire Mountain Country Store, 24.1km away, features charming local goods.

Recreation

Lake Mansfield Park, a tranquil retreat 11.3km from Sheffield, offers serene walking trails and picturesque views, perfect for relaxation. Music Mountain, located 20.9km away, hosts vibrant concerts, while Undermountain Golf Course, 14.5km from town, provides an invigorating outdoor experience for golf enthusiasts.

Adventure

At Ski Butternut, 8.0km from Sheffield, experience exhilarating skiing amidst a vibrant sports atmosphere. The Housatonic River Walk, located 9.7km away, offers breathtaking scenery for hikers seeking outdoor adventure. For thrill-seekers, Catamount Aerial Adventure Park, 12.9km from Sheffield, features an exciting zipline and ropes course.

Nightlife

In Sheffield, the Mahaiwe Performing Arts Center offers a charming atmosphere with captivating performances just 9.7km away. Infinity Music Hall and Bistro, located 17.7km away, blends exquisite dining with live entertainment. For a rich cultural experience, the Berkshire Theatre Festival is only 19.3km from Sheffield.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

Booking tips and Expedia advantages for Sheffield

To save money on your trip to Sheffield, consider visiting during the off-peak months of January and March to April, when accommodation prices are lower. Booking your stay for a Tuesday can also help you find cheaper rates, while Saturdays tend to be the most expensive. Use Expedia’s search tool to filter by budget, location, and hotel type, including eco-certified options. You can further save by bundling your hotel, flights, and activities into a package deal, ensuring you get the best value for your stay.

  • The most and least expensive months on average to stay in a hotel: The cheapest months to stay in Sheffield are January and March to April, where the prices are slightly lower. This is in comparison to July to August and October, where prices are slightly higher.
  • The most and least expensive days on average to stay in a hotel: The least expensive day to stay in Sheffield is Tuesday. The most expensive day to stay in Sheffield is Saturday.
  • Find cheap hotels on Expedia: Expedia’s search tool enables you to set your budget, choose your ideal location, and much more. You can arrange your search results to display prices from lowest to highest, allowing you to find the most affordable hotels first. Additionally, you can refine your choices by hotel type; for instance, selecting the Eco-certified filter will showcase sustainable and environmentally friendly hotels available for booking.
  • Consider bundling your trip: You can save money by combining your hotel reservation in Sheffield with your flights and activities through an Expedia package.

Find the best attractions near Sheffield

Sheffield, Massachusetts, is an excellent destination for adventure seekers and outdoor enthusiasts, offering a variety of activities such as skiing and exploring nature. Visitors can enjoy nearby national parks, nature reserves, and picturesque lakes, making it ideal for eco-friendly experiences. Whether you’re hiking, skiing, or simply soaking in the natural beauty, Sheffield promises an unforgettable outdoor vacation.

  • Bash Bish Falls State Park: Located 11.3km away from Sheffield, this stunning park features breathtaking waterfalls surrounded by lush greenery. It offers a perfect blend of adventure and tranquillity, with hiking trails that lead you through picturesque landscapes.
  • Housatonic River: Just 9.7km from Sheffield, the Housatonic River is a serene spot ideal for picnicking and scenic walks. Its beautiful banks provide a peaceful atmosphere where you can enjoy the natural beauty and perhaps spot some local wildlife.
  • Three Mile Pond Wildlife Management Area: Only 3.2km from Sheffield, this nature reserve is an eco-friendly haven. It's perfect for outdoor enthusiasts seeking adventure, with opportunities for birdwatching and exploring diverse habitats.

Best time to go to Sheffield

The best time to visit Sheffield is dependent on what kind of holiday you are seeking. July is its hottest month on average. At this time, visitor numbers are slightly high and weather is mostly sunny with light rain. January is its coolest month on average. At this time, visitor numbers are average and weather is mostly cloudy with light rain.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January23.2°F (-4.9°C)Light RainMostly CloudyAverageSlightly Low
February24.8°F (-4.0°C)Light RainMostly CloudySlightly LowAverage
March32.5°F (0.3°C)Light RainMostly CloudyAverageSlightly Low
April44.2°F (6.8°C)Light RainMostly CloudyAverageSlightly Low
May55.9°F (13.3°C)Light RainMostly SunnyAverageAverage
June63.7°F (17.6°C)Light RainMostly SunnySlightly HighAverage
July69.8°F (21.0°C)Light RainMostly SunnySlightly HighSlightly High
August67.8°F (19.9°C)Light RainMostly SunnyAverageSlightly High
September60.8°F (16.0°C)Light RainMostly SunnySlightly HighAverage
October49.8°F (9.9°C)Light RainMostly SunnyAverageSlightly High
November37.8°F (3.2°C)Light RainMostly SunnySlightly LowAverage
December29.7°F (-1.3°C)Light RainMostly CloudySlightly LowAverage

The nearest major airports for your trip to Sheffield

To visit Sheffield, Massachusetts, you can fly into several major airports. Hartford, CT (BDL-Bradley Intl.) is 59.5km away, with nearby hotels such as the Sheraton Hartford Hotel at Bradley Airport and The Capitol Hotel, both offering convenient access via airport shuttles. Albany, NY (ALB-Albany Intl.) is 80.5km distant, featuring hotels like Oakcliff Bed and Breakfast and Four Points by Sheraton Albany, easily reachable from the airport. Finally, Newburgh, NY (SWF-Stewart Intl.) is 91.7km away, with options like The Crossroads Hotel and Comfort Suites Fishkill, both accessible via local transportation services. Each airport provides a variety of accommodation choices to enhance your stay.

Frequently asked questions

Where is the best place to stay in Sheffield?
Wilder House Berkshires is one of the top choices for your stay based on our traveller data. This B&B offers free breakfast and free parking. Two other options for your trip to the area are Berkshire Mountain Lodge and Holiday Inn Club Vacations Oak n' Spruce Resort in the Berkshires by IHG. See all available top hotels, or vacation rentals in Sheffield.
If I need to cancel my hotel reservation in Sheffield, will I receive a refund?
Yes, the majority of hotel reservations are fully refundable provided that you cancel prior to the hotel's cancellation deadline, which in most cases is within 24 or 48 hours of your arrival date. If your reservation is non-refundable, it may still be possible to cancel it and be given a refund within 24 hours of booking. Filter your search by fully refundable to find flexible hotel deals in Sheffield.
What are some accommodation options with pools in Sheffield?
Berkshire Mountain Lodge: Features free self parking, an indoor pool and complimentary wireless Internet access. Holiday Inn Club Vacations Oak n' Spruce Resort in the Berkshires by IHG and The Yankee, Trademark Collection by Wyndham are a couple of other choices that feature an on-site pool. View all hotels with pools in Sheffield.
What's it like staying in Sheffield?
Visitors can enjoy all that Sheffield has to offer, including the casinos and local tours. In Sheffield, there are 32 hotels and other accommodation options to choose from. Find out more about Sheffield.
What are the top places to visit in Sheffield?
Favourite places to visit include Magnolia Bluffs Casino, Housatonic River and Ashley House. A couple of additional sights to add to your itinerary are Mount Everett State Reservation and Thom Reed UFO Monument Park. Take a look at what more there is to see and do in Expedia's Sheffield guide.
What's the seasonal weather like in Sheffield?
The hottest months are usually July and August, with an average temperature of 19°C, while the coldest months are January and February, with an average of -2°C. The snowiest months in Sheffield are January, March, February and November, with each month seeing an average of 18 cm of snowfall.

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